Coloring-matters of the anthraquinone series.



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No Drawin g.

To allwhom it may concern:

Be it known. that I, .MAX IIENRYISLER,

citizen of the Swiss Republic, residing at Mannheim, .Germany, have invented new :and useful Improvements in Coloring-Matproducts can be used as vat coloring mat ters. :To obtain theseprpdu'c'ts I condense 'ouiega dichlor 2 -.met1:v1- anthraquinre or anthraquinone-2-aldehyde, or a halogen derivative of either: of these bodies, with ortho-dialnino anthraquinones; 1.2 diamino- 'anthraquinone and 2.3-diamino-anthraquinone can be used for the purpose. The 1.2- diamiuo-anthraquinonc can be obtained either by .the reduction of Iamino-'2-nitroanthraquinone or by. splitting oil' the sulfo group from l.2-diamino-anthraquinone-3- sult'oacid, as has hitherto been practised, or the 1.2-diamino-anthraquinone can be obtained by heating l-amino-anthraquinoneleulfoacid with ammonia under pressure.

For the purposes of this invention an anthraqi|inone-Q-aldehyde body is'to be regarded as equivalent to the corresponding o1i'lega-dihalogen 2 methyl anthraquinone body.

The condensationto the new products is elfected by heating the two components to gether, preferably m a suitable solvent or suspension agent. The products obtained vary slightly according to the conditions applyingduring the reaction, thus products can be obtained which appear to stand in a relation to one another similar to that in which the imidazole stands to its dihydro compound. The product obtained by the condensation of 1.Q-diaminwanthraqdinone and anthraquinone-2-aldehyde, as .hereinafter setjorth in Example 4, gives, upon this constitution.

, oononme ivm'rrnns on'rnn ANT RA' UINONE snn'rns.

Specification of Letters Patent. JPatented lIgjy 27 1913, Application filed'April 20, 1912. Serial No. e92,043., i

analysis, figures which correspond to the formula but obviously. the percentage composition as deternnnedby analysis cannot give oertain information as to the: composition of the products and I do not bindmyself to The f ollowing are examples of how my invention can be carried into practical effeet, but the invention is not confined to these examples. The parts are by weight.

: Example 1: Mix together 24 parts of 1.2-

diamino-anthraquinone, 30 parts of o1negadichlor-2-methyl-anthraquinone, 500 parts of nitrobenzene, 15 parts of c'alcined'soda and 1.2 part of copper oxid.- Boil the mixture until a further increase in the formation of coloring matter can no longer be observed. Collect the coloring matter by filtration, which is preferably effected at about (3., Wash with nitrobenzene and subsequently with alcohol. If desired, purify the product by boiling with acetic acid, which removes some of the impurities,.if

any be present, and re-crystallize from. 'quinolin. The product purified in this'way does not melt at 330 C. andis almost, or entirely, insoluble in most of the usual solvents, though it can be rel-crystallized from boiling quinolin; It dissolves in concentrated sulfuric acid, giving a solutionv ofa yellow-orange color. In an alkaline hydro- .sulfite solution it gives a yellow-red vat ble in water, caustic soda, and dilute min-.

eral acid, and soluble in concentrated sulfuric acid giving a yellow solution. In a1- kaline sodium hydrosulfite solution a brownred vat is obtained which dyes cotton brownred, but, upon washing and exposure to the air, the color becomes a clear lemon yellow.

Example Mix 10 parts of 1.2-diaminoanthraquinone, 20 parts of anthraquinone 2-aldehyde and -300'parts of nitrobenzene (or an equal weight of naphthalene) and heat the mixture at the boiling point for some hours. Isolate as described .in the foregoing Example 1. This product also dyes from the alkaline hydrosulfite vat giv: ing yellow shades on cotton. It gives a yellow solution in concentrated sulfuric acid. An analogous coloring -matter, giving a red solution in concentrated sulfuric acid, can be obtained in the same way from 2.3- diamQno-anthraquinone.

Example4: Mix 10 parts of 1.2-diarninoanthraquinone, from 11 to 14 parts of anthraquinone-Q-aldehyde and 200 parts of pyridin, and boil the mixture till no further separation of crystals of the condensation product can be observed. After filtering off the paste of crystals, wash with alcohol.

The coloring matter is obtained directlyin a pure condition. It yiel ds a greenish yellow solution in concentrated sulfuric acid and dyes cotton from an alkaline hydro" sulfite vat giving violet shades. If, in this example, the i1.2-diamino-anthraquinone be replaced by the isomeric 2.3-diamino-an thraquinonc, a coloring matter obtained which dyes cotton shades of orange color and yields a yellow solution in concentrated sulfuric acid. Other solvents can be em ployed instead of pyridin, for instance naphthalene and nitrobenzene, but then care must be taken that the temperature does not rise above about from 115 to 120 6., as

at higher temperature the coloring matter described in the foregoing Example 3 is formed. Cotton which has been dyed violetshades by means of the coloring matter obtainable to this example turns boiled with nitrobenzene.

Example 5: Mix 10 parts of 1.2-diaminoyellow when .anthraquinone, 20 parts of o1nega-dichlor-2- methyl-anthraquinone and 200 parts of pyridin, and boil the mixture for some time in a vessel provided with an inverted .condenser. A coloring matter similar in shade to, the violet coloring matter described in Example 4: separates out. If, instead of 1.2- diamino-anthraquinone, in this example, the isomeric 2.3 diamino-anthraquinone he treated in accordance with this example, a product is obtained which dyes cotton, from a hydrosulfite vat, yellow shades, and which ives a redsolution in concentrated suluric acid.

Now what I clalm 1s:-

1. The process of producing coloring mat- 4. Thenew vat coloring matters of the anthraquinone series which are condensation products of an omega-dihalogen-Q-methylanthraquinone body with an ortho-diaminoanthraquinone, which new coloring matters are insoluble in water and in dilute acids and alkalis and yield from yellow to red solutions in sulfuricacid, from yellow-red to brown-red vats with alkaline hydrosulfite, and dye cotton from such vats yellow to orange to violet shades.

5. The new vat coloring matter of the anthraquinone series which is a condensation product of 1.2-diamino'anthraquinonc with. omega dichlor 2 methyl anthraquinone, which new coloring matter is insoluble in water and in dilute acids and alkalis, is infusible below 330 (7., gives a yellow-orange solution in concentrated sulfuric acid. a yellow-red vat with alkaline hydrosulfite so lution, and dyes cotton clear yellow shades.

In testimony whereof I have hereunto set my hand in the presence of two subscribing witnesses.

MAX HENRY ISLER. \Vitnesses ERNEST F. Ennimiin'r, Josnrii Prmrrmr.

Copies of this patent may be obtained for five cents eaclnby addressing the Commissioner of Patents Washington, I). c. 

